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> the pattern I've seen time and time again is Developers thinking the previous generation had no idea what they were doing and they'll do it way better. They usually nail the first 80%, then hit a new edge case not well handled by their architecture/model

Perfect, I've seen this happen many times as well. I think you're generous on the 80% part. Usually they nail the first 50%, but they time they get to 80% its getting just as messy and some of the developers are planning another rewrite again.




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